EP0652216A2 - Dérivés d'aldéhyde salicylique et d'acide salicylique de pyridine, procédés pour leur préparation et leur utilisation comme herbicides - Google Patents

Dérivés d'aldéhyde salicylique et d'acide salicylique de pyridine, procédés pour leur préparation et leur utilisation comme herbicides Download PDF

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Publication number
EP0652216A2
EP0652216A2 EP94116720A EP94116720A EP0652216A2 EP 0652216 A2 EP0652216 A2 EP 0652216A2 EP 94116720 A EP94116720 A EP 94116720A EP 94116720 A EP94116720 A EP 94116720A EP 0652216 A2 EP0652216 A2 EP 0652216A2
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Prior art keywords
alkyl
alkoxy
alkylthio
group
haloalkoxy
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EP94116720A
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German (de)
English (en)
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EP0652216B1 (fr
EP0652216A3 (fr
Inventor
Joachim Dr. Rheinheimer
Uwe Josef Dr. Vogelbacher
Ernst Dr. Baumann
Matthias Dr. Gerber
Karl-Otto Dr. Westphalen
Helmut Dr. Walter
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BASF SE
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BASF SE
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the present invention relates to substituted pyridylsalicylaldehyde and salicylic acid derivatives of the general formula I.
  • WO 91/13065 and DE-A 39 19 435 have salicylaldehyde or salicylic acid derivatives with an unsubstituted pyridyl radical a herbicidal action.
  • Corresponding compounds with specially substituted pyridyl radicals such as 6-methyl-2-pyridyl, 3-chloro-5-pyridyl and 5-chloro-2-pyridyl are also disclosed in the latter document.
  • the action of the compounds known from the literature is not always satisfactory with regard to herbicidal action, the bioregulatory action and / or selectivity, and therefore the task was to provide pyridyl-substituted or -salicylic acid derivatives with improved activity.
  • R 1 particularly preferably represents a group OR 9 .
  • Substituted pyridylsalicylaldehyde and salicylic acid derivatives of the formula I according to Claim 1 in which at least two of the radicals R 15 to R 17 are hydrogen are particularly preferred.
  • R 3 is methoxy and X is CH or CF or in which R 3 together with X form an OCH 2 CH 2 chain.
  • Aromatic carboxylic acid derivatives of the formula I are obtained, for example, by using a corresponding aromatic carboxylic acid derivative of the formula II, which is accessible according to the examples given below, with a corresponding compound of formula III in the presence of a base.
  • R 20 means chlorine, bromine, iodine, aryl or alkylsulfonyl such as. B. toluenesulfonyl or methylsulfonyl or another equivalent leaving group.
  • Compounds of the formula IV with a reactive substituent R 20 are known in most cases or are easy to obtain with the general specialist knowledge.
  • alkali metal or alkaline earth metal hydrides such as NaH, or CaH 2
  • alkali metal hydroxides such as NaOH or KOH
  • alkali metal alcoholates such as potassium tert-butoxide
  • alkali metal carbonates such as Na 2 C0 3 or K 2 CO 3
  • alkali metal amides such as NaNH 2 or lithium diisopropylamide or tertiary amines such as Triethylamine or pyridine are used.
  • a phase transfer catalyst can be added if this promotes sales.
  • crown ethers or organic ammonium compounds are suitable.
  • solvents such as dimethyl sulfoxide, dimethylformamide, tetrahydrofuran, methyl t-butyl ether, diethyl ether, acetone, methyl ethyl ketone, toluene, benzene, dimethoxyethane, dioxane, pyridine or t-butanol.
  • the reaction temperatures are generally between -80 and 150 ° C, preferably between -10 and 130 ° C.
  • This implementation which is the subject of simultaneous German application No. P 43 37 321.6, can be represented by the following reaction scheme:
  • the reaction of the cyclic acetals IV with the salt V and the further reaction with the heterocycle of the formula III can be carried out directly in a reaction vessel up to the active ingredient I.
  • the salt R I 'M is first added, which can also be prepared in situ from a compound R 1 ' H and a base. Then you add the heterocycle III.
  • the addition of III should advantageously only take place when the first step of the reaction, the addition of the salt V to the intermediate IV, has largely been completed. This can take between a few minutes and several hours, the reaction temperature being between -40 ° C and 200 ° C, usually between 0 ° C and 130 ° C.
  • Polar solvents e.g. B. ethers such as diethyl ether, methyl tert-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, amides such as dimethylformamide, dimethylacetamide, N-methylpyrrolidone, dimethylpropyleneurea or dimethyl sulfoxide.
  • a phase transfer catalyst such as a crown ether or a quaternary ammonium salt can be added if this promotes sales.
  • the reaction temperature is between -40 and 200 ° C, preferably between 0 and 160 ° C.
  • the reaction times are usually between a few minutes and 50 hours, usually 0.5-10 hours.
  • 0.8 to 3, in particular 0.9 to 1.5, mol equivalents of the compound V (R 1 'M) are generally used per mole of starting material IV.
  • the amount of heterocycle III is likewise expediently 0.8 to 3, in particular 0.9 to 1.5 molar equivalents, based on I.
  • the reaction can be carried out continuously or batchwise; at atmospheric pressure, overpressure or underpressure.
  • a suitable work-up method consists, for example, of mixing the reaction mixture, from which the solvent can also be partially or completely evaporated beforehand, with water and filtering the product or extracting it with an organic solvent.
  • A is a halogen atom, for example chlorine, bromine, iodine, C 1 -C 4 haloalkylsulfonyloxy, in particular trifluoromethylsulfonyloxy, C1-C4-alkylsulfonyloxy or fluorosulfonyloxy.
  • the starting materials are generally known or are accessible in a generally known manner.
  • a dehydrating agent can be added to bind the water formed in the reaction, e.g. Mol sieve, acid anhydrides such as trifluoroacetic anhydride, acetic anhydride, sodium sulfate, calcium chloride, if this promotes sales.
  • a reactive acetal of the compound 0 CR'R ", such as, for example, a dimethyl acetal, diethyl acetal, ethylene acetal or propylene acetal, is also suitable.
  • catalysts are acidic ion exchangers, protonic acids, such as, for example, toluenesulfonic acid, sulfuric acid, phosphoric acid, etc., or Lewis acids, such as Aluminum chloride, titanium tetrachloride, zinc chloride, calcium chloride, magnesium chloride, tin chloride, etc. Often the water formed or the alcohol formed from the acetal can be distilled off directly from the reaction mixture.
  • protonic acids such as, for example, toluenesulfonic acid, sulfuric acid, phosphoric acid, etc.
  • Lewis acids such as Aluminum chloride, titanium tetrachloride, zinc chloride, calcium chloride, magnesium chloride, tin chloride, etc.
  • the water formed or the alcohol formed from the acetal can be distilled off directly from the reaction mixture.
  • W is trialkylstannyl, for example tri-C 1 -CG-alkylstannyl as trimethylstannyl, triethylstannyl, Tripropylstannyl, tributylstannyl, Tripentylstannyl or Trihexylstannyl, dihydroxyboranyl, Dialkoxyboranyl, for example, di-C 1 -C 4 -alkoxyboranyl as Dimethoxyboranyl, Diethoxyboranyl, Dipropoxyboranyl, or di Diisopropoxyboranyl -
  • the boron or tin compounds used are either known or can be prepared analogously to known compounds.
  • a catalytically active palladium compound is used in this new process.
  • Any palladium salts or complexes which are at least partially soluble in the reaction mixture are suitable.
  • the oxidation state of the palladium can be 0 or 2.
  • the palladium salts include a. the following counterions are considered: chloride, bromide, iodide, sulfate, acetate, trifluoroacetate, acetylacetonate or hexafluoro-2,4-pentadionate.
  • Many different palladium complexes can be used. The only requirement is that the ligands on the palladium can be displaced from the substrate under the reaction conditions. Phosphine ligands such as. B.
  • aryl alkyl phosphines such as u. a. Methyldiphenylphosphine, isopropyldiphenylphosphine, triarylphosphines such as u. a. Triphenylphosphine, tritolylphosphine, trixylylphosphine, trihetarylphosphines such as trifurylphosphine or dimeric phosphines.
  • Olefinic ligands such as u. a. Dibenzylidene acetone or its salts, cycloocta-1,5-diene or amines such as trialkylamines (e.g. triethylamine, tetramethylethylene diamine, N-methylmorpholine) or pyridine.
  • the complex used can be used directly in the reaction. So you can z. B. with tetrakistriphenylphosphine palladium (0), bistriphenylphosphine palladium dichloride, bistriphenylphosphine palladium diacetate, a dibenzylideneacetone palladium (0) complex, tetrakismethyldiphenylphosphine palladium (0) or bis (1,2-diphenylphosphino dichloride).
  • a palladium salt and, in addition, a suitable ligand can also be used, which then only form the catalytically active complex in situ. This procedure offers z. B. in the above salts and phosphine ligands such. B.
  • trifurylphosphine or tritolylphosphine Palladium complexes such as. B. tris (dibenzylidene acetone) dipalladium, bis (dibenzylidene acetone) palladium or 1,5-cyclooctadiene palladium dichloride by the addition of ligands such as. B. trifurylphosphine or tritolylphosphine can be activated further.
  • the amount of W-Py, based on the starting material IV-A, is generally 0.8 to 3, preferably 0.95 to 1.5 molar equivalents.
  • the reaction temperature is between -20 and 200 ° C, preferably between 50 and 160 ° C.
  • the reaction times are usually between a few minutes and 50 hours, usually 0.5-10 hours. When using low-boiling solvents, it is sometimes useful to carry out the reaction under autogenous pressure in the autoclave.
  • the carboxylic acid derivatives listed in claim 2 can be used, for. B. also be prepared by first converting the carboxylic acid in the usual way into an activated form such as a halide or imidazolide and then reacting it with the corresponding hydroxyl compound of the formula R 1 -H. These two steps can also be simplified, for example, that the carboxylic acid in the presence of a dehydrating agent such as. B. a carbodiimide or a suitable phosphonic anhydride can act on the hydroxyl compound.
  • a dehydrating agent such as. B. a carbodiimide or a suitable phosphonic anhydride
  • carboxylic acids of the formula I can also be converted to many of the esters described as follows: the carboxylic acid is first converted into a salt - in particular an alkali metal salt - and then further - if appropriate in the presence of one of the salts bases mentioned above - with an alkylating agent for reaction.
  • the alkylating agent has the general formula R 'R 2' wherein R 2 ', the usual leaving groups such as chlorine, bromine, iodine, aryl or alkylsulfonyl such.
  • the alkylating agents used are generally known or they can be prepared analogously to known compounds.
  • the compounds 1 or the compositions containing them and their environmentally compatible salts for example of alkali metals and alkaline earth metals, can be used as herbicides in crops such as wheat, rice, corn, soya and Cotton combats weeds and grass weeds very well without damaging crops, an effect that occurs especially at low application rates.
  • the compounds 1 or the herbicidal compositions comprising them can be sprayed, atomized, for example in the form of directly sprayable aqueous solutions, powders, suspensions, and also high-strength aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, sprays or granules , Dusting, scattering or pouring.
  • the application forms depend on the purposes; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.
  • the compounds I are generally suitable for the preparation of directly sprayable solutions, emulsions, pastes or oil dispersions.
  • Mineral oil fractions of medium to high boiling point such as kerosene or diesel oil, furthermore coal tar oils as well as oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, alkylated benzenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone or strongly polar solvents, such as N-methylpyrrolidone or water.
  • Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water.
  • the substrates as such or dissolved in an oil or solvent can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers.
  • concentrates consisting of an active substance, wetting agent, tackifier, dispersant or emulsifier and possibly solvent or oil, which are suitable for dilution with water.
  • alkali, alkaline earth, ammonium salts of aromatic sulfonic acids e.g. Lignin, phenol, naphthalene and dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, as well as salts of sulfated hexa-, hepta- and octadecanols as well as fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives Formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl, octyl or nonylphenol, alkylphenol, tributylphenyl polyglycol
  • Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
  • Granules e.g. Coated, impregnated and homogeneous granules can be produced by binding the active ingredients to solid carriers.
  • Solid carriers are mineral earths such as silica gel, silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, Ammonium nitrate, ureas and vegetable products such as corn flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.
  • mineral earths such as silica gel, silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics
  • the formulations generally contain between 0.01 to 95% by weight, preferably between 0.5 to 90% by weight, of active ingredient.
  • the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).
  • the herbicidal compositions or the active compounds can be applied pre- or post-emergence. If the active ingredients are less compatible with certain crop plants, application techniques can be used in which the herbicidal compositions are sprayed with the aid of sprayers in such a way that the leaves of the sensitive crop plants are not hit as far as possible, while the active ingredients are applied to the leaves of undesirable plants growing below them or the uncovered floor area (post-directed, lay-by).
  • the application rates of active ingredient are 0.001 to 2.0, preferably 0.01 to 1.0 kg / ha of active substance (a.S.).
  • the compounds 1 according to the invention or compositions containing them can also be used in a further number of crop plants for eliminating undesired plants.
  • the following crops are considered, for example:
  • the compounds of formula I can further influence the various stages of development of a plant and can therefore be used as growth regulators.
  • the variety of effects of plant growth regulators depends above all on the type and variety of plants; the time of application, based on the development stage of the plant, and the season; the place and method of application (e.g. seed dressing, soil treatment, leaf application or trunk injection in trees); climatic factors (e.g. temperature, amount of precipitation, day length and light intensity); soil conditions (including fertilization); on the formulation or application form of the active ingredient and on the concentrations of the active substance used.
  • the vegetative growth of the plants can be strongly inhibited, which manifests itself in particular in a reduction in the growth in length.
  • a reduced intensity of the growth of grasses on roadsides, hedges, canal embankments and on lawns such as parks, sports and orchards, ornamental lawns and airfields has proven to be advantageous in practice, so that the labor-intensive and costly lawn cutting can be reduced.
  • the growth regulators can save cutting costs.
  • the alternance of fruit trees can be broken by growth regulators.
  • growth regulators can also increase or inhibit the lateral branching of the plants. There is interest in this, e.g. if in tobacco plants the formation of side shoots (stinging shoots) should be inhibited in favor of leaf growth.
  • frost resistance can also be significantly increased in winter rape.
  • the growth in length and the development of a lush (and therefore particularly susceptible to frost) leaf or plant mass are inhibited.
  • the young rapeseed plants are held back after sowing and before the onset of winter frosts, despite favorable growth conditions in the vegetative development stage. This also eliminates the risk of frost for plants that tend to prematurely degrade flowering and switch to the generative phase.
  • Winter cereals are advantageous if the stocks are well planted in autumn by treatment with compounds according to the invention, but do not go into the winter too abundantly.
  • additional yields can be achieved both on parts of plants and on plant ingredients. For example, it is possible to induce the growth of larger quantities of buds, flowers, leaves, fruits, seeds, roots and tubers, to increase the sugar content in sugar beets, sugar cane and citrus fruits, to increase the protein content in cereals or soybeans or to grow rubber trees to stimulate the increased latex flow.
  • the compounds of formula I can increase yields by interfering with the plant metabolism or by promoting or inhibiting vegetative and / or generative growth.
  • both a shortening or lengthening of the development stages and an acceleration or delay of the ripeness of the harvested plant parts can be achieved before or after the harvest.
  • Ease of harvest for example, is of economic interest, which is made possible by the time-related falling or decreasing of the adhesive strength on the tree in the case of citrus fruits, olives or other types and varieties of pome, stone and nuts.
  • the same mechanism that is, the promotion of the formation of separating tissue between the fruit or leaf and shoot part of the plant is also essential for a well controllable defoliation of useful plants such as cotton.
  • the intensity of the irrigation can be reduced and thus more economical management can be carried out.
  • growth regulators there is a better use of the available water because, among other things, the opening width of the stomata is reduced, a thicker epidermis and cuticle are formed, the root penetration of the soil is improved and the microclimate in the crop is favorably influenced by a more compact growth.
  • the compounds I are particularly suitable for shortening the stalks of crop plants such as barley, rapeseed and wheat.
  • the growth regulators of the formula I to be used according to the invention can be added to the crop plants both from seeds (as seed dressings) and via the soil, i.e. through the root and - particularly preferably - by spraying over the leaf.
  • the preparation of the agents is carried out analogously to that of herbicides (see above).
  • the amount of active ingredient is not critical due to the high tolerance to plants.
  • the optimal application rate varies depending on the target, season, target plants and growth stages.
  • the pyridylsalicylic acid derivatives I can be used with numerous representatives of other herbicidal or growth-regulating agents Active ingredient groups are mixed and applied together.
  • Active ingredient groups are mixed and applied together.
  • diazines, 4H-3,1-benzoxazine derivatives, benzothiadiazinones, 2,6-dinitroanilines, N-phenyl carbamates, thiol carbamates, halocarboxylic acids, triazines, amides, ureas, diphenyl ethers, triazinones, uracils, benzofuran derivatives, cyclohexane derivatives are used as herbicidal mixture partners -dione derivatives which carry a carboxy or carbimino group in the 2-position, quinolinecarboxylic acid derivatives, imidazolines, sulfonamides, sulfonylureas, aryloxy-, heteroaryloxyphenoxypropionic
  • the oily product is taken up in 2 l of methyl tert-butyl ether, mixed with 2 l of water and 2 l of saturated NaHC0 3 solution and stirred for 1.5 h. It is separated off, extracted with methyl tert-butyl ether, the combined organic phases are washed with brine, dried over sodium sulfate and concentrated. The residue is stirred with 200 ml of n-pentane, suction filtered and dried. Yield: 115 g (90%). Mp 60-62 ° C.
  • acetone oxime dissolved in 30 ml of toluene, are mixed with 1.66 g of a 30% sodium methylate solution in methanol and concentrated in vacuo. 35 ml of dimethylformamide and then 2.50 g of 2,2-dimethyl-5- (2-methoxypyridin-5-yl) -4H- (1,3) benzodioxin-4-one are added, the mixture is stirred for 15 minutes at room temperature and finally added 1.90 g of 4,6-dimethoxy-2-methylsulfonylpyrimidine was added.
  • the active ingredients suspended or emulsified in water were applied directly after sowing using finely distributing nozzles.
  • the tubes were lightly sprinkled to promote germination and growth and then covered with clear plastic hoods until the plants had grown. This cover causes the test plants to germinate evenly, provided that this has not been impaired by the active ingredients.
  • test plants For the purpose of post-emergence treatment, the test plants, depending on the growth habit, were first grown to a height of 3 to 15 cm and only then treated with the active ingredients suspended or emulsified in water. For this purpose, the test plants were either sown directly and grown in the same containers or they were first grown separately as seedlings and transplanted into the test containers a few days before the treatment.
  • the application rate for post-emergence treatment was 0.0313 and 0.0625 kg / ha a.S.
  • the plants were kept at temperatures of 10 - 25 ° C or 20 - 35 ° C depending on the species.
  • the trial period lasted 2 to 4 weeks. During this time, the plants were cared for and their response to each treatment was evaluated.
  • the herbicidal activity was rated on a scale from 0 to 100. 100 means no emergence of the plants or complete destruction of at least the aerial parts and 0 means no damage or normal growth.
  • the growth-regulating effect was determined by measuring the length. At the end of the test, the growth heights of the treated plants were measured and related to the growth height of untreated plants.
  • the plants used in the greenhouse experiments are composed of the following types:

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
EP94116720A 1993-11-02 1994-10-24 Dérivés d'aldéhyde salicylique et d'acide salicylique de pyridine, procédés pour leur préparation et leur utilisation comme herbicides Expired - Lifetime EP0652216B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE4337323A DE4337323A1 (de) 1993-11-02 1993-11-02 Substituierte Pyridylsalicylaldehyd- bzw. salicylsäurederivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide
DE4337323 1993-11-02
US08/332,723 US5783521A (en) 1993-11-02 1994-11-01 Substituted pyridylsalicylaldehyde or -salicylic acid derivatives, their preparation and their use as herbicides

Publications (3)

Publication Number Publication Date
EP0652216A2 true EP0652216A2 (fr) 1995-05-10
EP0652216A3 EP0652216A3 (fr) 1995-05-17
EP0652216B1 EP0652216B1 (fr) 2001-02-28

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EP94116720A Expired - Lifetime EP0652216B1 (fr) 1993-11-02 1994-10-24 Dérivés d'aldéhyde salicylique et d'acide salicylique de pyridine, procédés pour leur préparation et leur utilisation comme herbicides

Country Status (8)

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US (1) US5783521A (fr)
EP (1) EP0652216B1 (fr)
JP (1) JP3541067B2 (fr)
CN (1) CN1107846A (fr)
CA (1) CA2134625C (fr)
DE (2) DE4337323A1 (fr)
ES (1) ES2155459T3 (fr)
HU (1) HU215280B (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997012883A1 (fr) * 1995-10-02 1997-04-10 Basf Aktiengesellschaft Produits intermediaires et procede de production de derives substitues d'acide salicylique utiles comme agents phytosanitaires
WO1997015560A1 (fr) * 1995-10-25 1997-05-01 Basf Aktiengesellschaft Derives d'acide salicylique des types sulfoxyde et sulfone, procede de production correspondant et leur utilisation comme herbicides

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4337322A1 (de) * 1993-11-02 1995-05-04 Basf Ag Pyrid-N-oxid substituierte Salicylaldehyd- bzw. Salicylsäurederivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide
DE19536809A1 (de) * 1995-10-02 1997-04-03 Basf Ag Heterocyclisch substituierte Salicylsäurederivate
DE19602404A1 (de) * 1996-01-24 1997-07-31 Basf Ag Sulfoxid- und Sulfon-substituierte Heterocyclen, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide
JP2002524399A (ja) 1998-09-09 2002-08-06 石原産業株式会社 除草剤として有用な縮合ベンゼン誘導体
US6649566B2 (en) 2001-12-13 2003-11-18 Morse Enterprises Limited, Inc. Stabilized concentrated formulations for enhancing plant defensive responses
JP5406032B2 (ja) * 2007-10-26 2014-02-05 クミアイ化学工業株式会社 サトウキビ用糖度向上剤及びこれを用いたサトウキビの登熟促進方法
CN104370875B (zh) * 2014-09-25 2018-11-13 深圳波顿香料有限公司 一种乙基香兰素1,2-丙二醇缩醛的制备方法
JPWO2023243677A1 (fr) * 2022-06-17 2023-12-21

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HU9403134D0 (en) 1995-01-30
EP0652216B1 (fr) 2001-02-28
ES2155459T3 (es) 2001-05-16
CN1107846A (zh) 1995-09-06
JPH07188217A (ja) 1995-07-25
US5783521A (en) 1998-07-21
HUT69738A (en) 1995-09-28
DE4337323A1 (de) 1995-05-04
JP3541067B2 (ja) 2004-07-07
CA2134625C (fr) 2006-03-21
DE59409663D1 (de) 2001-04-05
EP0652216A3 (fr) 1995-05-17
HU215280B (hu) 1998-11-30
CA2134625A1 (fr) 1995-05-03

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